#------------------------------------------------------------------------------
#$Date: 2022-09-04 01:56:11 +0300 (Sun, 04 Sep 2022) $
#$Revision: 277615 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/11/7711138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7711138
loop_
_publ_author_name
'Griffin, Samuel E.'
'Adamczyk, Olivia V.'
'Schafer, Laurel L.'
_publ_section_title
;
 Vanadium Pyridonates: Dimerization, Redox Behaviour, and Metal-Ligand
 Cooperativity
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02177C
_journal_year                    2022
_chemical_formula_moiety         'C16 H24 N4 O2 V'
_chemical_formula_sum            'C16 H24 N4 O2 V'
_chemical_formula_weight         355.33
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-12 deposited with the CCDC.	2022-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                77.6800(10)
_cell_angle_beta                 87.3910(10)
_cell_angle_gamma                89.4980(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9184(5)
_cell_length_b                   9.1750(5)
_cell_length_c                   11.3271(6)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.27
_cell_volume                     904.57(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker-Nonius Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22197
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.565
_diffrn_reflns_theta_min         1.842
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0632 before and 0.0413 after correction. The Ratio of minimum to maximum transmission is 0.9381. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       irregular
_exptl_crystal_F_000             374
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         5531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0380P)²+0.3445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4847
_reflns_number_total             5531
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02177c3.cif
_cod_data_source_block           ls857_a
_cod_database_code               7711138
_shelx_shelxl_version_number     2018/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.845
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C5(H5), C12(H12), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,
 H14C), C16(H16A,H16B,H16C), C9(H9A,H9B,H9C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.75437(2) 0.32804(2) 0.20258(2) 0.01292(6) Uani 1 1 d . . . . .
O1 O 0.78303(10) 0.54996(9) 0.16887(8) 0.01755(17) Uani 1 1 d . . . . .
O2 O 0.69973(10) 0.14393(10) 0.32844(8) 0.01796(17) Uani 1 1 d . . . . .
N1 N 0.58415(11) 0.45875(11) 0.28434(9) 0.01658(19) Uani 1 1 d . . . . .
N3 N 0.93243(11) 0.28184(11) 0.12704(9) 0.01651(19) Uani 1 1 d . . . . .
N4 N 0.62911(11) 0.29542(12) 0.08411(10) 0.0174(2) Uani 1 1 d . . . . .
N2 N 0.86572(12) 0.29618(12) 0.37742(9) 0.0189(2) Uani 1 1 d . . . . .
C1 C 0.66479(13) 0.58107(13) 0.23246(11) 0.0158(2) Uani 1 1 d . . . . .
C2 C 0.62404(14) 0.72556(14) 0.24647(11) 0.0185(2) Uani 1 1 d . . . . .
C7 C 0.78700(14) 0.16843(14) 0.41191(11) 0.0184(2) Uani 1 1 d . . . . .
C6 C 0.45783(14) 0.47262(15) 0.35040(11) 0.0208(2) Uani 1 1 d . . . . .
H6 H 0.401049 0.385918 0.385803 0.025 Uiso 1 1 calc R . . . .
C4 C 0.49435(16) 0.73567(15) 0.31598(12) 0.0236(3) Uani 1 1 d . . . . .
H4 H 0.462782 0.830519 0.328643 0.028 Uiso 1 1 calc R . . . .
C3 C 0.71643(16) 0.85726(14) 0.18402(13) 0.0244(3) Uani 1 1 d . . . . .
H3A H 0.822874 0.835736 0.197440 0.037 Uiso 1 1 calc GR . . . .
H3B H 0.686907 0.944508 0.216638 0.037 Uiso 1 1 calc GR . . . .
H3C H 0.700005 0.877780 0.097066 0.037 Uiso 1 1 calc GR . . . .
C5 C 0.40861(15) 0.60955(16) 0.36805(12) 0.0244(3) Uani 1 1 d . . . . .
H5 H 0.318723 0.618003 0.414419 0.029 Uiso 1 1 calc R . . . .
C8 C 0.80088(16) 0.07197(16) 0.52658(12) 0.0253(3) Uani 1 1 d . . . . .
C13 C 1.07001(14) 0.36113(16) 0.13934(12) 0.0233(3) Uani 1 1 d . . . . .
H13A H 1.046042 0.443994 0.179057 0.035 Uiso 1 1 calc GR . . . .
H13B H 1.117061 0.400161 0.059052 0.035 Uiso 1 1 calc GR . . . .
H13C H 1.139323 0.292497 0.188183 0.035 Uiso 1 1 calc GR . . . .
C15 C 0.65997(16) 0.32520(17) -0.04599(12) 0.0263(3) Uani 1 1 d . . . . .
H15A H 0.591261 0.402323 -0.085735 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.645658 0.233587 -0.075525 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.763772 0.359748 -0.064401 0.040 Uiso 1 1 calc GR . . . .
C12 C 0.96421(15) 0.33434(18) 0.45139(13) 0.0269(3) Uani 1 1 d . . . . .
H12 H 1.020895 0.423509 0.425388 0.032 Uiso 1 1 calc R . . . .
C14 C 0.96136(16) 0.16784(16) 0.05745(13) 0.0261(3) Uani 1 1 d . . . . .
H14A H 1.031927 0.094368 0.099524 0.039 Uiso 1 1 calc GR . . . .
H14B H 1.004652 0.214193 -0.022703 0.039 Uiso 1 1 calc GR . . . .
H14C H 0.867029 0.118076 0.048585 0.039 Uiso 1 1 calc GR . . . .
C16 C 0.47734(15) 0.23798(17) 0.11521(13) 0.0269(3) Uani 1 1 d . . . . .
H16A H 0.466655 0.143670 0.088925 0.040 Uiso 1 1 calc GR . . . .
H16B H 0.404930 0.310547 0.074637 0.040 Uiso 1 1 calc GR . . . .
H16C H 0.458370 0.221097 0.202977 0.040 Uiso 1 1 calc GR . . . .
C9 C 0.71011(19) -0.06885(17) 0.55888(14) 0.0332(3) Uani 1 1 d . . . . .
H9A H 0.604753 -0.044305 0.573854 0.050 Uiso 1 1 calc GR . . . .
H9B H 0.748187 -0.133004 0.631911 0.050 Uiso 1 1 calc GR . . . .
H9C H 0.718056 -0.121264 0.491991 0.050 Uiso 1 1 calc GR . . . .
C10 C 0.90253(18) 0.1152(2) 0.60051(13) 0.0350(4) Uani 1 1 d . . . . .
H10 H 0.916792 0.053685 0.677997 0.042 Uiso 1 1 calc R . . . .
C11 C 0.98499(17) 0.2468(2) 0.56461(14) 0.0352(4) Uani 1 1 d . . . . .
H11 H 1.053997 0.275527 0.616941 0.042 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 145.82(4) . . ?
O1 V1 N1 63.02(4) . . ?
O1 V1 N2 92.45(4) . . ?
O1 V1 C1 30.95(4) . . ?
O1 V1 C7 121.26(4) . . ?
O2 V1 N1 90.47(4) . . ?
O2 V1 N2 62.83(4) . . ?
O2 V1 C1 119.67(4) . . ?
O2 V1 C7 30.79(4) . . ?
N1 V1 N2 85.98(4) . . ?
N1 V1 C1 32.08(4) . . ?
N1 V1 C7 88.10(4) . . ?
N3 V1 O1 97.36(4) . . ?
N3 V1 O2 105.48(4) . . ?
N3 V1 N1 159.79(4) . . ?
N3 V1 N2 90.32(4) . . ?
N3 V1 C1 128.11(4) . . ?
N3 V1 C7 99.22(4) . . ?
N4 V1 O1 104.89(4) . . ?
N4 V1 O2 97.62(4) . . ?
N4 V1 N1 93.76(4) . . ?
N4 V1 N3 96.26(5) . . ?
N4 V1 N2 160.43(4) . . ?
N4 V1 C1 101.41(4) . . ?
N4 V1 C7 128.41(5) . . ?
N2 V1 C1 88.74(4) . . ?
N2 V1 C7 32.04(4) . . ?
C1 V1 C7 106.52(4) . . ?
C1 O1 V1 97.30(7) . . ?
C7 O2 V1 97.28(7) . . ?
C1 N1 V1 87.02(7) . . ?
C6 N1 V1 153.20(9) . . ?
C6 N1 C1 119.77(11) . . ?
C13 N3 V1 119.70(8) . . ?
C14 N3 V1 129.23(9) . . ?
C14 N3 C13 111.00(10) . . ?
C15 N4 V1 127.88(8) . . ?
C15 N4 C16 110.98(11) . . ?
C16 N4 V1 121.11(9) . . ?
C7 N2 V1 87.03(8) . . ?
C12 N2 V1 152.82(10) . . ?
C12 N2 C7 120.02(12) . . ?
O1 C1 V1 51.76(6) . . ?
O1 C1 N1 112.64(10) . . ?
O1 C1 C2 124.76(11) . . ?
N1 C1 V1 60.89(6) . . ?
N1 C1 C2 122.61(11) . . ?
C2 C1 V1 176.36(9) . . ?
C1 C2 C3 119.96(11) . . ?
C4 C2 C1 116.12(12) . . ?
C4 C2 C3 123.88(12) . . ?
O2 C7 V1 51.93(6) . . ?
O2 C7 N2 112.85(11) . . ?
O2 C7 C8 124.69(12) . . ?
N2 C7 V1 60.92(6) . . ?
N2 C7 C8 122.46(13) . . ?
C8 C7 V1 176.49(11) . . ?
N1 C6 H6 119.2 . . ?
N1 C6 C5 121.64(12) . . ?
C5 C6 H6 119.2 . . ?
C2 C4 H4 119.2 . . ?
C2 C4 C5 121.54(12) . . ?
C5 C4 H4 119.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 C5 C4 118.31(12) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C7 C8 C9 119.63(13) . . ?
C10 C8 C7 115.90(14) . . ?
C10 C8 C9 124.45(13) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C12 H12 119.3 . . ?
N2 C12 C11 121.33(15) . . ?
C11 C12 H12 119.3 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10 119.1 . . ?
C8 C10 C11 121.73(14) . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 118.54(14) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 2.0064(9) . ?
V1 O2 2.0116(9) . ?
V1 N1 2.2169(10) . ?
V1 N3 1.8581(10) . ?
V1 N4 1.8580(11) . ?
V1 N2 2.2182(11) . ?
V1 C1 2.5339(12) . ?
V1 C7 2.5347(12) . ?
O1 C1 1.3137(14) . ?
O2 C7 1.3080(16) . ?
N1 C1 1.3477(15) . ?
N1 C6 1.3442(16) . ?
N3 C13 1.4590(16) . ?
N3 C14 1.4527(16) . ?
N4 C15 1.4542(17) . ?
N4 C16 1.4574(16) . ?
N2 C7 1.3466(17) . ?
N2 C12 1.3393(17) . ?
C1 C2 1.4109(16) . ?
C2 C4 1.3831(18) . ?
C2 C3 1.4963(18) . ?
C7 C8 1.4170(18) . ?
C6 H6 0.9500 . ?
C6 C5 1.3786(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.398(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C5 H5 0.9500 . ?
C8 C9 1.499(2) . ?
C8 C10 1.377(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C11 1.380(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.394(3) . ?
C11 H11 0.9500 . ?
